How did you get started in the sports world?
It was late November freshmen year, and I was playing basketball. I don’t remember how, but it came to my attention that George Steinbrenner was a Williams alum. I said, ‘What the heck? Let’s take a shot.’ So I wrote him this long, cheesy letter where I talked about the leaves changing colors in Williamstown and what a great time of year it was. I lied and said I was a Yankees fan. I grew up a hardcore Mets fan. I asked for an internship or whatever he could do.
The next day I realized that I didn’t have an address to send the letter to. So I emailed the President at the time, Morty Schapiro, and said, ‘hey, I have this letter. Do you happen to have Mr. Steinbrenner’s address?’ Within a couple of hours Morty wrote back to me. He said, ‘this sounds like a great idea, I’d love to help you out. I know George myself. Why don’t you bring the letter to my office, and I’ll send him a letter with your letter and make sure it gets to him.’
I did that the next day and within a week I had a couple of calls from the Yankees, saying they wanted me to come down to do some interviews. I ended up going down the first week of spring break. We won the national championship in basketball on Saturday. Monday morning I went in to New York. I met with a few people and toured around. At the end, I met with the COO who said, ‘Mr. Steinbrenner’s already signed off on your internship. Where would you like to work?’
I chose baseball operations. That summer I started with the Yankees, interning for the General Manager Brian Cashman. I was the only intern, which was great because I got to have my hand in everything. Coming from Williams was great for that because you learn to be a part of everything because the focus is on being a complete student. Brian and I developed a pretty good relationship. He brought me back in the summers of 2004 and 2005 and then hired me full-time when I graduated in 2006.
My first year was a lot of faxing and filing, getting cups of coffee – the traditional intern stuff. But for me it was great to get in on the ground floor. When you’re doing that kind of stuff you get a good feel for the administrative aspect of it.
In 2007 I switched into the scouting department. I left the Yankees this past March, but at the time, I was running the department and felt really good about where I was at. I always knew that I wanted to work in sports, but if you were to tell me that I was going to have one job in one place for ten years and that all of it was because of the Williams alumni network, I would have told you that was pretty cool.
People come to me now and ask what’s your secret, what’s your advice for getting in the door. I say, ‘get lucky.’ No matter what school you went to, use your alumni network. Not only was Mr. Steinbrenner an alum, but having the President of your school take a chance on you and respond within an hour to help you out, that’s pretty special. He didn’t know me before that.
In March you moved to the MLS. What encouraged you to make that move?
I’ve always been a huge soccer fan – soccer and basketball were always my number 1 and 2 sports. They’re both total team sports, and your teammates can make you better or worse. When I was at Williams, I was fortunate to play with some of the most talented guys I’d played with, but what set us apart is that we were good together. We were unselfish. We knew where each person was going to be.
I felt like I was getting to a point where I needed to say, ‘this is going to be the rest of your life in baseball or now would be the time to make a move to a different sport.’
Now I’m here as the Director of Player Relations. My primary job is to negotiate contracts for the league and for the teams that I manage. I manage 8 teams and am in charge of their salary budgets, their rosters, making sure they’re cap compliant and that the salaries they’re offering make sense. I work on the scouting network as we grow as a league.
It’s different going from the team side to the league side. With the team, you are just focused on yourself and how you’re going to win. With the league, you have to make sure everyone is in line and playing by the same rules.
You clearly love sports. What gets you fired up about the professional side?
With the Yankees it was easy. When you wake up and you know that not only do you have one of the best teams in the game but you also have a chance to get better. The chance to go out and compete every day was the same as it was during my time at Williams. Some of the best basketball we ever played was not in the games, it was during practice. The chance to go out and compete and be around hyper-competitive guys is amazing – it’s addictive.
Now, we don’t have the same sense of winning and losing. It’s a different excitement, but the league is growing exponentially. Everyday we’re attacking a new problem and thinking about how we can improve and grow soccer. We have a new collective bargaining agreement coming up, and it’s the perfect time to think about what we want the next 5 years of the league to look like. Every day there’s so much room for growth and learning – there’s always a new challenge – and I’m loving it.
Does the MLS feel like a start-up in the sense that you’re building something almost from the ground up?
No doubt. I came from one of the most established places. There’s so much energy here and there’s so much to do that it’s almost like we’re drinking from the fire hose at times. We’ve seen after this past world cup, that we’re poised for a takeoff. I really think there’s a chance for something special to happen with the MLS.
What inspired you to send the letter? Did you know that you wanted it to turn into a career?
As soon as you get to Williams it’s apparent that it’s a different place. There’s a special sense of community and brotherhood. You get a weird comfort level with people you haven’t met because everyone basically has the same experience. I knew I loved sports and Mr. Steinbrenner was the first prominent alum that I’d heard about, so I figured why not take a shot. It was a combination of saying what the heck and trusting in the special environment that Williams creates. I played that up in my letter. It’s a special place. To tell someone who went to Williams that you went there or you’re there now really resonates. I know it did for Mr. Steinbrenner. He approved my internship before I even got there.
Did you talk with Mr. Steinbrenner?
Ya I did. Interns weren’t supposed to talk to him at all, but I got the courage and did talk to him. I thanked him every chance I got.
Even though you were working for the Yankees, you weren’t doing totally glamorous stuff. How were you able to stay on track with where you wanted to end up in the organization?
It’s almost like being a freshman at Williams. I took a lot of political science and sociology classes that year. I had to read 200-300 pages between classes. The way to survive was to do the work as best you could but also to ask the right questions in class so you could get some guidance. It was similar with the Yankees. There was always more work you could do, but when you had the opportunity to sit with someone who worked there full-time, you could take advantage of that. All the things I did in my discussion classes at Williams, helped me with how to think on my feet, how to ask the right questions, how to look at problems for the first time and begin to solve those on the fly.
Are there stories from your early days at the Yankees where you realized it was something you could do for a long time?
100% in 2003 – that first summer. In mid-July, I’d been there for 5 or 6 weeks. It was a Friday night, and we were playing Oakland. We had a rain delay, and when you have a rain delay, you sort of just sit around the office. It was 10:15, and they hadn’t called the game yet. The four people in the department were all sitting in the GM’s office just shooting the breeze. I thought, ‘this is pretty cool. I’m talking baseball with the GM and assistant GM, and we’re looking at different players and different contracts.’
We had a very demanding owner in Mr. Steinbrenner, but that kept us on our toes. He wanted us to do our best, to be the best. That’s kind of what got me going at Williams. I’m a competitive guy – that obsession with being as good as you can possibly be defined my experience with the Yankees. That rain delay in July it all clicked. I realized that there was a reason I liked it so much – it was similar to the experience I put myself through at Williams.
The Yankees were challenging, but in many ways it was less overwhelming than biology at Williams.
At the end of the first summer, Brian asked me to come back and I said, ‘yes absolutely.’ That was one of the happiest moments of my life.
How have you come to define success?
I’ve always been one for personal goals. It’s cliché, but working hard is a goal of mine. Going to bed knowing that I gave it my all that day, it’s a big goal. I’ve learned that I’m my harshest critic. I need to make sure that I believe I’m working hard and doing everything that I can be doing.
Success is a result. It’s like in The Shawshank Redemption, you’re tunneling through the walls with a spoon thinking, ‘this is never going to break.’ I felt that way when I was trying to get a job with the MLS. Williams students are coming from the top of wherever they are. It’s difficult to be a one-dimensional Williams student. You’re so used to being surrounded by all of these amazing people that you take for granted how amazing everyone is. Excellence becomes average – it becomes your standard.
What advice would you give to a current Williams student preparing to go into the real world?
The biggest piece of advice especially for people trying to break into sports is to market yourself – write letters, put yourself out there – and don’t get discouraged. That’s the most important thing. You’re always going to hear no more than you hear yes. You can’t get frustrated. You have to keep going. Cherish the internships. It’s the best opportunity to learn. You might be doing grunt work, but you should pay attention to every detail: what are you faxing, what letters are you sending. That’s how you learn.
Also reach out to the alumni network, tell your story, and be open to anything. There’s not one set path. I wouldn’t have thought that ten years in baseball would end up in a career in soccer. Constantly look to build on your skill set, always keep an eye for how this is helping your grow. That might help you make the next jump. Also, keep in touch with people. Openings spring up at various times.
We won the World Series with the Yankees in 2009. Sometime in 2010, we were talking about the level of focus that we had during the season of 2009, especially during the playoffs. I remember saying to someone that if didn’t feel as strange as I thought it would because I remembered the focus we brought to the NCAA tournament games at Williams. It sounds crazy to compare division 3 basketball games to the World Series, but it’s that same kind of feeling, that same attention to detail.